A new strategy for the synthesis of aryl- and heteroaryl-substituted exocyclic olefins from allyl alcohols using PBr3

Treatment of aryl and heteroaryl substituted allyl alcohols 7-14 with phosphorus tribromide at 0 degrees C furnished a new series of substituted exocyclic olefins 15-22 in good yields. The +I inductive effect of substituents on the aryl group is described. (c) 2005 Elsevier Ltd. All rights reserved.

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 51; pp. 8849 - 8852
Main Authors Shagufta, Parai, MK, Panda, G
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 19.12.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
phosphorous tribromide
ALKENES
aryl-substituted exocyclic olefin
PROSTACYCLIN
EFFICIENT SYNTHESIS
REACTIVITY
STEREOSPECIFIC SYNTHESIS
HIGHLY STEREOSELECTIVE-SYNTHESIS
allyl alcohol
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Summary:Treatment of aryl and heteroaryl substituted allyl alcohols 7-14 with phosphorus tribromide at 0 degrees C furnished a new series of substituted exocyclic olefins 15-22 in good yields. The +I inductive effect of substituents on the aryl group is described. (c) 2005 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2005.10.081